HCID 59343384, compound → (3R,3aR,6aR)-hexahydro-2H-furo[3,2-b]pyrrol-3-ol

HRID 16195Notes

Reaction equation

HRID 16195 reaction equation
[OH:1][C@@H:2]1[C@H:6]2[N:7](C(OCC3C4C=CC=CC=4C4C3=CC=CC=4)=O)[CH2:8][CH2:9][C@H:5]2[O:4][CH2:3]1.O[C@@H]1[C@H]2N(C(OC(C)(C)C)=O)CC[C@H]2OC1>Cl.O1CCOCC1>[O:4]1[C@H:5]2[C@H:6]([NH:7][CH2:8][CH2:9]2)[C@@H:2]([OH:1])[CH2:3]1

Participants

5

Reactant 2

HCID 59343384HCID 59343384, compoundHCID 66986914tert-butyl (3R,3aR,6aR)-3-hydroxy-hexahydro-2H-furo[3,2-b]pyrrole-4-carboxylate

Product 1

HCID 55287552(3R,3aR,6aR)-hexahydro-2H-furo[3,2-b]pyrrol-3-ol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Preparation of (3R,3aR,6aR)-(9H-fluoren-9-yl)methyl 3-hydroxytetrahydro-2H-furo[3,2-b]pyrrole-4(5H)-carboxylate (2b). Alcohol (2f) (558 mg, 2.43 mmol) was dissolved in 4M HCl in dioxane (14.06 mL) and left to stand at ambient temperature for 1 h. The solvent was removed in vacuo and the residue azeotroped from toluene (3×20 mL) to give hydrochloride salt of (3R,3aR,6aR)-hexahydro-2H-furo[3,2-b]pyrrol-3-ol (2 g) used directly in the following step.

Workup

  1. waitleft
  2. customThe solvent was removed in vacuo
  3. customthe residue azeotroped from toluene (3×20 mL)

Sources & evidence

ORD record
ord-46b6e0c75d42419c97542f1bd2e16994
Source dataset
uspto-grants-2010_06
Patent number
US07737150B2

Reaction notes

Loading…